Justice Clarence Thomas has been friends with Dallas real estate magnate Harlan Crow since the mid-1990s, after Thomas joined the U.S. Supreme Court.

Since then, Crow, a Republican campaign donor, has bankrolled several projects that relate to the justice, the New York Times reports. Crow paid $175,000 to help finance a library project dedicated to Thomas. He paid $500,000 for Thomas’ wife, Virginia, to start a conservative group. And he paid to restore a cannery in Thomas’ hometown of Pin Point, Ga., that included a museum about the history of the town.

In the case of the cannery and museum, the owner had told Thomas he hoped it could be preserved, which led Thomas to put him in touch with Crow, the story says.

The company that bought the cannery for $1.5 million is controlled by a partnership run by Crow. The preliminary construction budget was $1.3 million. Thomas participated in a documentary for the museum, met with a design team working on the project, and helped choose people working on it.

According to the Times, the museum project “raises the sharpest questions yet—both about Justice Thomas’s extrajudicial activities and about the extent to which the justices should remain exempt from the code of conduct for federal judges.”

The code, which is not binding on the Supreme Court, says judges should not “personally participate” in raising money for charitable endeavors.

The Times interviewed two ethics experts, who differed on the propriety of the museum project. Stanford law professor Deborah Rhode said Thomas should not be directly involved in fund-raising activities, no matter how worthy. Chapman University law professor Ronald Rotunda said the situation was “peculiar,” but “I don’t think I could say it’s unethical.” The fund-raising ban is intended to deter judges from pressuring donors, rather than relying on a rich friend, Rotunda said.